methyl 4-<<(4-fluoro-2-nitrophenyl)amino>methyl>benzoate | 133052-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-<<(4-fluoro-2-nitrophenyl)amino>methyl>benzoate
• 英文别名: methyl 4-N-(4-fluoro-2-nitrophenyl)aminomethylbenzoate；Methyl 4-[[(4-fluoro-2-nitrophenyl)amino]methyl]benzoate；methyl 4-[(4-fluoro-2-nitroanilino)methyl]benzoate
• CAS: 133052-61-6
• 化学式: C₁₅H₁₃FN₂O₄
• 分子量: 304.278
• InChiKey: MHXDDEXKFOULTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-<<(4-fluoro-2-nitrophenyl)amino>methyl>benzoate 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  New nonpeptide angiotensin II receptor antagonists. 1. Synthesis, biological properties and structure-activity relationships of 2-alkylbenzimidazole derivatives

  摘要：

  On the basis of an extension of the literature lead 1, a series of benzimidazoles have been synthesized and shown to be angiotensin II (AII) receptor antagonists. The structure-activity relationships of these new antagonists have been explored and the key binding interactions defined. Molecular mechanics calculations were carried out on analogues of imidazole AII antagonists and conformationally restricted analogues were synthesized. The benzimidazole antagonists displaced AII in binding studies in vitro with IC50 values in the range 10(-5)-10(-7) M and antagonized the hypertensive effects of AII in vivo (rats) following intravenous administration with ED50 values in the range of 5-20 mg/kg.

  DOI：

  10.1021/jm00083a011
• 作为产物：
  描述：

  4-氨甲基苯甲酸甲酯 、 2,5-二氟硝基苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以70%的产率得到methyl 4-<<(4-fluoro-2-nitrophenyl)amino>methyl>benzoate
  参考文献：
  名称：

  New nonpeptide angiotensin II receptor antagonists. 1. Synthesis, biological properties and structure-activity relationships of 2-alkylbenzimidazole derivatives

  摘要：

  On the basis of an extension of the literature lead 1, a series of benzimidazoles have been synthesized and shown to be angiotensin II (AII) receptor antagonists. The structure-activity relationships of these new antagonists have been explored and the key binding interactions defined. Molecular mechanics calculations were carried out on analogues of imidazole AII antagonists and conformationally restricted analogues were synthesized. The benzimidazole antagonists displaced AII in binding studies in vitro with IC50 values in the range 10(-5)-10(-7) M and antagonized the hypertensive effects of AII in vivo (rats) following intravenous administration with ED50 values in the range of 5-20 mg/kg.

  DOI：

  10.1021/jm00083a011

文献信息

• Benz[4,5]imidazole-containing angiotensin antagonists
  申请人：Imperial Chemical Industries plc

  公开号：US05171748A1

  公开（公告）日：1992-12-15

  The invention concerns novel heterocyclic compounds of the formula I as defined herein and their physiologically acceptable salts, together with pharmaceutical compositions containing them. The heterocyclic compounds antagonize the actions of angiotensin II and are of value in treating diseases or medical conditions such as hypertension and congestive heart failure in warm-blooded animals. The invention further includes processes for the manufacture of the novel compounds and their use in medical treatment.

  这项发明涉及本文所定义的式I的新颖杂环化合物及其生理学上可接受的盐，以及含有它们的药物组合物。这些杂环化合物拮抗血管紧张素II的作用，在治疗温血动物的高血压和充血性心力衰竭等疾病或医疗状况方面具有价值。该发明还包括用于制造这些新化合物的工艺和它们在医疗治疗中的应用。
• US5171748A
  申请人：——

  公开号：US5171748A

  公开（公告）日：1992-12-15
• New nonpeptide angiotensin II receptor antagonists. 1. Synthesis, biological properties and structure-activity relationships of 2-alkylbenzimidazole derivatives
  作者：Andrew P. Thomas、Christopher P. Allott、Keith H. Gibson、John S. Major、Brian B. Masek、Alec A. Oldham、Arnold H. Ratcliffe、David A. Roberts、Simon T. Russell、Douglas A. Thomason

  DOI：10.1021/jm00083a011

  日期：1992.3

  On the basis of an extension of the literature lead 1, a series of benzimidazoles have been synthesized and shown to be angiotensin II (AII) receptor antagonists. The structure-activity relationships of these new antagonists have been explored and the key binding interactions defined. Molecular mechanics calculations were carried out on analogues of imidazole AII antagonists and conformationally restricted analogues were synthesized. The benzimidazole antagonists displaced AII in binding studies in vitro with IC50 values in the range 10(-5)-10(-7) M and antagonized the hypertensive effects of AII in vivo (rats) following intravenous administration with ED50 values in the range of 5-20 mg/kg.